Doing Business, Part 31 (Patreon)

The 14th Annual Seattle Leadership Conference is pleased to welcome Gabrielle Heller.

Gabrielle Heller, CEO of [Company Name Redacted], will be joining the SLC for two panels on Saturday, April 2nd. In the first, “Future Paths,” Ms. Heller will be joined by a panel of executives from a wide range of companies to discuss the new directions business is taking as technology continues to evolve at a breakneck pace.

Later in the day, be sure to catch Ms. Heller’s second panel: “Relationships Within Command,” a deep look at her strategies in building a team that works together as a family, instead of just co-workers.

***

I felt as if I had been reborn. Maybe I had been.

The night before had been transcendent–feeling like the culmination of every single moment that had passed since the first time I ran into Gabrielle Heller in a random hallway while I tried to hang an award on the wall.

I awoke from a perfect sleep, finding that Mommy’s arms and legs were still wrapped around me, keeping my body close to hers under the covers. She wore nothing, while I just wore a diaper.

My diaper was completely soaked, and I had no recollection of when that happened. But it didn’t bother me. I barely even considered it. Why should I? This was what I did now. I liked the feeling of the swampy diaper pressed between her body and mine.

“Ah, the little boy has awakened,” she cooed to me.

My eyes darted to hers, not realizing that she was also awake. It actually made the moment feel even more special, knowing that she had chosen to stay in bed, clutching me close to her, even though she had been awake for who-knows how long.

“H-hello,” I said, my voice cracking and straining at its first use of the day.

“Sleep well?”

I nodded. “Yes. Very.”

“I wish I could stay in bed with you all day…”

“You can,” I said. “You should.”

“I have to be at the conference today,” she said. “They’d be a little bitter if I didn’t show up.”

“Will you be there all day?”

“Most of it,” she said. “But the good news is that this is the only day I have to be there. Starting tonight, I’m all yours.”

“N-no,” I corrected. “Mommy, I’m all yours.”

“Of course,” she said, laughing. “Always.”

She kissed me on the forehead, setting off a chain reaction of warm and pleasurable feelings throughout my body.

“What about me?” I asked–a half-cooked question that probably didn’t have enough context to make sense.

“What about you, Baby?”

“What should I do today while you’re at the conference?”

“Be a baby,” she cooed, running her fingers through the hair on the back of my head. “What else is there to do?”

“But…”

“I know. The prospect of being a little baby, all alone in a strange city, is probably a little overwhelming, yes? Not to mention boring.”

I nodded. Honestly, it was the boredom I was concerned about more than anything else. I wasn’t about to go toddling through the streets of Seattle in my thick diaper, but I also wasn’t sure how I was going to keep myself amused–especially when my cock remained sealed up in its cage.

“I’m sure I could find a way to spice up your day for you.”

This made me a little nervous, yet–as always–excited. I bet she could. And, knowing her, she already had a few ideas.

“First things first,” she said, patting the bottom of my sodden diaper. “We need to get you changed into something a little fresher, yes?”

“Yes, Mommy. Please.”

She released me from her grip, and I begrudgingly released her from mine. She slipped out of the bed and wrapped herself up in a thick terry cloth bathrobe. I was disappointed to see her cover up, but it was probably a good thing for my ever-strained cock.

It was no new revelation that Mommy had gotten diaper changes down to a perfect and efficient science. Yet this never seemed to detract from how much I loved them. The way she manhandled my legs. The effortlessness of her almost every movement. The way the baby wipes would zip across my skin, or how she knew the exact amount of powder to shake onto my skin. She was a wizard.

“Now that we’re out of the office,” she said, opening up her suitcase as my hands pawed at the loudly crinkly fresh diaper, “I feel like we finally have the chance to dress you in something more age-appropriate.”

My heart began pounding, as I could only imagine what she was going to reveal to me.

It was a sailor outfit. A navy blue onesie, with white trim that circled the sleeves and leg bands, a white-trimmed collar, and–the start of the show–a bright red tie.

“Is this not the cutest thing?”

My burning cheeks should’ve been enough of an answer, though I added: “Y-yes, Mommy.”

Truthfully? I loved it. Adored it, even. The deeper I fell into the baby abyss, the deeper I hoped to fall. Yes. Dress me up like a little baby.

“Aww, look at you,” she cooed. “Practically wiggling around in excitement, aren’t you?”

“I, uhm, I really want to wear that for you, Mommy.”

“You’re such a good boy.”

Soon, I was being led to the mirror by the hand so that I could see myself. There I was, in just my sailor onesie and a thick diaper. I probably would’ve looked quite babyish in just the onesie, but the puffy bulk of the diaper seemed to turn that dial to 11. She popped my pacifier into my mouth, completing the look.

I was just a baby.

Then, a peculiar thing happened–the hotel room’s phone rang. In the age of cellphones and laptops, I found it hard to believe that any landlines were ever being used–let alone one in a hotel room.

Mommy flashed me a mischievous grin as she walked to the phone and selected the button to answer it on speakerphone.

“Good morning, this is Edward from the concierge desk. Mr. Ashburn has a guest. I wanted to check with you before allowing them up.”

I felt my face grow white as I glanced back into the mirror. Who? Who was this and why were they looking for me?

“Does he now?” Mommy replied with an air of mock-confusion. “And who is this visitor?”

“This is Kylie Feldman.”

If possible, I became even whiter. My pacifier dropped out of my mouth and into my hand.  “H-how did she…”

“Send her up,” Mommy confidently said into the phone before ending the call.

“Mommy… How did she know where we were staying? I…I thought that…”

“You were quite sleepy after your big night,” she said. “You passed right out. So, of course, I took it upon myself to pick up your pants and I found the piece of paper she wrote her phone number on. And, remembering what you told me last night, I thought maybe I should reach out to her.”

“I don’t know if she should see me like this,” I said, looking into the mirror again. Yup, still a big infant.

“I don’t think it’ll matter,” she said, shrugging. “But why don’t you stay in here for a few.”

She left the bedroom, closing the door part way behind her. It was open enough that I could hear her walking through the living room, though it seemed to conceal me from any curious eyes that would come through the main entrance to our suite. Mommy seemed not to care that she would be greeting Kylie in just her bathrobe.

If Kylie thought something was going on between us before, wait until she sees this.

I had nothing but questions. Why did Mommy reach out to Kylie? What did she say to her? Why had Mommy agreed to let Kylie come here, of all places, while I was dressed like this.

There was a knock at the door. Fuck.

All I could do was listen.

“Good morning, Kylie,” Mommy said moments after opening the door.

“Oh, er, hi Ms. Heller. I…didn’t realize you were…here.” Kylie’s voice still carried those notes of sweet and cattiness, but it also sounded deflated.

“Surprised? Likewise, imagine my surprise to see that you’re stopping by.”

“I…was supposed to meet your assistant Clark here. Are you two…sharing a room?”

“We’re sharing lots of things these days,” Mommy said. “Like phone numbers.”

“Oh.” There was a lot of uncertainty in Kylie’s voice.

“Why don’t you come inside, Kylie.”

For a moment, I wasn’t sure if Kylie had come in or not. For all I knew, she had sprinted off down the hallway, never to return. All I could hear was the sound of the door closing again. I caught another glimpse of myself in the mirror. Still a baby. I kind of hoped that she had run for the hills.

But then I heard Kylie’s voice again: “Look, I didn’t want to start any trouble. I just thought that he could…”

“I know what you wanted,” Mommy said. “You were texting with me late last night, not him.”

“Look, I said a lot of things that…” her voice trailed off before she started again: “I thought I was talking to Clark.”

“I know,” Mommy said.

“You can’t tell my Mom,” she said. “Please?” Kylie sounded desperate. I wondered what else she had said to Mommy last night, thinking it was me.

“You graduated high school, yes?” Mommy asked her. “You’re over 18?”

“Yes.”

“So, you’re an adult. You have the right to beg boys for alcohol, while promising sexual favors in return. You have the right to send photos of your ass and tits to anyone you’d like to.”

My eyes widened. I really missed quite the conversation.

“But…my mother…”

“Ah, yes,” Mommy said. “Your mother–Gretchen–she’d disapprove, wouldn’t she? Probably cut you off from her credit cards. Maybe reconsider whatever investment she was making with Cornell to get you in as a student.”

“Please, don’t…”

“I see no reason to drag your mother into this conversation,” Mommy said. “I think we can help each other out.”

My heart was pounding even harder. What the hell did she mean by that?

“How so?” Kylie asked, sounding equally uncertain.

“Well, after I freshen myself up a bit, I’m going to be at the convention all day. And while I could take my darling assistant Clark with me, I think he’d be better off staying here.”

I looked in the mirror again. Yes. I was thinking that myself.

“But,” Mommy continued, “in Clark’s current state…I’m not sure I’d like to leave him to his own devices. He needs supervision.”

My heart sank. I could imagine where this was going…but it seemed far too surreal to actually be happening. Right?

Kylie laughed. “Are you asking me to…babysit your assistant? An adult man? Who is older than I am?”

“I’m encouraging you to stay here today,” Mommy replied. “You can call it whatever you’d like. But staying would ensure that our text messages stay between us. And, as long as you’re here…well, there’s a well-stocked fridge in the kitchen. If anything was to go missing…I probably wouldn’t even notice.”

“Sounds kind of like blackmail,” Kylie said.

“Funny. I had the same thought when Clark told me that you were asking for him to get you alcohol after you speculated about his relationship with me. So I don’t consider this to be blackmail, no. We’re just two people, doing favors for each other.”

My entire body felt tense as I braced myself for how Kylie would respond to this. I couldn’t begin to fathom the idea of Kylie seeing me like… I looked in the mirror again, feeling a shudder creep through my body.

“Fine,” Kylie said. “I guess I could stick around for a little while.”

“I thought you would.”

“He’s not going to do anything weird, is he?” Kylie asked.

Mommy laughed–a hearty bellow that suggested Kylie had inadvertently struck her funny bone. “I’m not going to lie to you, Kylie. Everything you see today is going to be weird.”

“Great.”

“Take a seat. I’m going to get myself ready for my day. Clark and I will be out in a few minutes.”

Without even realizing I had been moving, I found myself pressed to the other side of the partially-closed door–the single sheet of wood that, for now, protected the giant toddler from being spotted by Kylie. And soon, I won’t even have that. I scrambled back towards the bed as I heard Mommy walking back towards the bedroom.

“I suppose you heard that conversation?” she said, walking into the bedroom and closing the door behind her.

I nodded. I opened my mouth to say something, but I couldn’t imagine myself saying anything that she couldn’t tell just by looking at me.

“I know, I know,” she said, kissing my cheek as she floated past me to start getting some of her belongings from her suitcase. “This isn’t how you imagined today going, is it?”

I shook my head. “No, Mommy. Does she have to be here?”

“Two birds, one stone,” she said. “I wanted to hire a babysitter for you anyway. I thought it would’ve been fun. But then, of course, I got pretty busy and never got around to it. And I’m sure you can imagine just how hard it is to find a good babysitter willing to deal with such large diapers on short notice. And now, Miss Kylie seems to have just fallen into our lap.”

“But…” There were so many points to protest, where would I even start? I thought I’d pick the one that would, potentially, affect Mommy the most. “...aren’t you worried about her saying something to her mother?”

“No,” Mommy said, quite confidently. I expected her to have more to say, but that seemed to be it. Somehow, that simple answer felt plenty convincing to me, and I left it at that.

Still, I wasn’t even remotely thrilled about the prospect of having to not only reveal myself to Kylie, but to then spend the day with her.

“I don’t think she’ll change my diapers,” I said, an ever-so-slightly passive aggressive way of saying ‘I don’t think this is a good idea.’

“No, she probably won’t,” Mommy said with a shrug. “But that doesn’t mean that you can change your own either. I’ll take care of whatever she doesn’t when I get back.”

“But, what if…”

“You make a big mess in your diaper? You’ll probably stink up the whole suite. Oh well.”

There were many questions left, but only one I was going to ask: “Does it have to be this way?”

“Baby, if I say it’s going to be this way, then it’s going to be this way.”

I nodded.

“I’m going to take a shower and wash up, then get dressed and ready to go to the conference. You’re welcome to go out and greet Kylie yourself, if you’d like. But if you haven’t by the time I’m ready to go, I’m just going to drag you out there myself. I might even throw in an extra paddle or two on your padded bum. I can’t imagine you’d want her to see that.”

“M-maybe just a few more minutes, Mommy,” I said, feeling as pathetic as I probably looked.

She smiled. “Of course. But don’t keep your babysitter waiting too long.”

I sighed as I watched Mommy gather her things and strut into the bathroom. The last thing I saw, before the bathroom door closed behind her, was her robe falling to the ground, exposing her perfect body to me for just a moment.

I sighed a second time, grasping my thick diaper to feel my still-caged manhood within.

Behind one door was Mommy, naked and stepping into the shower. Heaven.

Behind the other was Kylie, completely unaware of the weird world she was about to be exposed to. Hell.

I’d have to go talk to Kylie before Mommy returned to the bedroom. But, considering that the water in the shower had just turned on, I had a few minutes.

I laughed to myself. Lyndie was going to get a kick out of this later.